WO2004021967A2 - Depigmenting composition for the skin comprising adapalene and at least one depigmenting agent - Google Patents

Depigmenting composition for the skin comprising adapalene and at least one depigmenting agent Download PDF

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Publication number
WO2004021967A2
WO2004021967A2 PCT/EP2003/010692 EP0310692W WO2004021967A2 WO 2004021967 A2 WO2004021967 A2 WO 2004021967A2 EP 0310692 W EP0310692 W EP 0310692W WO 2004021967 A2 WO2004021967 A2 WO 2004021967A2
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WO
WIPO (PCT)
Prior art keywords
depigmenting
skin
composition
adapalene
depigmenting agent
Prior art date
Application number
PCT/EP2003/010692
Other languages
English (en)
French (fr)
Other versions
WO2004021967A3 (en
Inventor
Isabelle Pelisson
André Jomard
Original Assignee
Galderma Research & Development, S.N.C.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to JP2004533511A priority Critical patent/JP4662769B2/ja
Application filed by Galderma Research & Development, S.N.C. filed Critical Galderma Research & Development, S.N.C.
Priority to EP03750634A priority patent/EP1536763B1/en
Priority to DK03750634T priority patent/DK1536763T3/da
Priority to DE60314887T priority patent/DE60314887T2/de
Priority to BRPI0313370-2A priority patent/BR0313370B1/pt
Priority to AU2003270272A priority patent/AU2003270272B2/en
Priority to MXPA05002064A priority patent/MXPA05002064A/es
Priority to CA002495043A priority patent/CA2495043A1/en
Priority to SI200330872T priority patent/SI1536763T1/sl
Publication of WO2004021967A2 publication Critical patent/WO2004021967A2/en
Priority to US11/042,519 priority patent/US20050163731A1/en
Publication of WO2004021967A3 publication Critical patent/WO2004021967A3/en
Priority to ZA2005/01753A priority patent/ZA200501753B/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

Definitions

  • Depigmenting composition for the skirt comprising adapalene and at least one depigmenting agent
  • the invention relates to a depigmenting composition for the skin comprising, in a physiologically acceptable medium, adapalene (6- [3- (1-adamantyl) -4-methoxyphenyl] - 2-naphthanoic acid) and at least one depigmenting agent and its pharmaceutical or cosmetic use.
  • the composition according to the invention may also contain a sunscreen.
  • A. M. Kligman describes, in patent
  • Retinoic acid (tretinoin) is known to have on its own a skin depigmenting activity (Guevara I. A. and Pandya A. G. Int. J. Dermatol . 40, 210-215 (2001) unlike adapalene which has no depigmenting activity as is, shown in Example 6 below.
  • adapalene which has no depigmenting activity as is, shown in Example 6 below.
  • a depigmenting agent in a depigmenting composition containing a sunscreen or not .
  • the applicant has discovered, surprisingly, that the combination of adapalene and a depigmenting agent made it possible to obtain a much more rapid depigmenting response than that obtained with the depigmenting agent alone.
  • the invention therefore relates to a depigmenting composition for the skin comprising, in a physiologically acceptable medium, adapalene and at least one depigmenting agent .
  • physiologically acceptable medium is understood to mean a medium compatible with the skin, the mucous membranes and/or the superficial body growths.
  • depigmenting agent is understood to mean any active agent having a skin depigmenting activity. This activity makes it possible to reduce the already existing pigmentation of the skin and also to prevent any additional pigmentation above the natural pigmentation.
  • depigmenting agent by way of nonlimiting example, phenolic derivatives, such as hydroquinone, hydroquinone monoethyl ether, hydroquinone monobenzyl ether or 4-hydroxyanisole; kojic acid and its derivatives; azelaic acid and its derivatives; linoleic acid; resorcinol and its derivatives; ellagic acid; hydroxy acids such as glycolic acid; ascorbic acid and its derivatives, in particular ascorbyl glucoside; zinc peroxide; and mercury chloride, arbutin and its derivatives such as those described in applications EP-895 779 and EP-524 109; aminophenol derivatives such as those described in applications WO 99/10318 and WO 99/32077, and in particular N-cholesteryloxy- carbonyl-para-aminophenol and N-ethyloxycarbonyl-para- aminophenol; iminophenol derivatives, in particular those described in application WO 99/22707; L-2-o
  • the invention also relates to a depigmenting composition for the skin comprising, in a physiologically acceptable medium, adapalene, at least one depigmenting agent and at least one sunscreen.
  • the composition according to the invention advantageously comprises between 0.0001 and 20% by weight of adapalene relative to the total weight of the composition and between 0.0001 and 20% by weight of depigmenting agent relative to the total weight of the composition, and preferably, respectively, between 0.001 and 10% by weight of adapalene relative to the total weight of the composition and between 0.025 and 10% by weight of depigmenting agent relative to the total weight of the composition.
  • the composition may also comprise at least one sunscreen in preferential concentrations ranging from 0.001 to 30.00% by weight relative to the total weight of the composition.
  • sunscreens there may be mentioned, by way of nonlimiting example, physical sunscreens such as titanium dioxide, zinc oxide, and chemical sunscreens such as octocrylene, ethylhexyl methoxycinnamate, octyl salicylate, avobenzone, oxybenzone, ecamsule or drometrizole trisiloxane or mixtures thereof .
  • Each sunscreen may be added at a concentration ranging from 0.001 to 20% by weight relative to the total weight of the composition.
  • compositions according to the invention may additionally comprise any additive customarily used in the cosmetic or pharmaceutical field, such as sequestrants, antioxidants, preservatives, fillers, electrolytes, humectants, colourings, customary inorganic or organic bases or acids, perfumes, essential oils, cosmetic active agents, moisturizers, vitamins, essential fatty acids, sphingolipids, self- tanning compounds, skin soothing and protecting agents such as allantoin.
  • any additive customarily used in the cosmetic or pharmaceutical field such as sequestrants, antioxidants, preservatives, fillers, electrolytes, humectants, colourings, customary inorganic or organic bases or acids, perfumes, essential oils, cosmetic active agents, moisturizers, vitamins, essential fatty acids, sphingolipids, self- tanning compounds, skin soothing and protecting agents such as allantoin.
  • additives may be present in the composition in an amount of 0.001 to 20% by weight relative to the total weight of the composition.
  • EDTA ethylenediaminetetraacetic acid
  • preservatives benzalkonium chloride, phenoxyethanol, benzyl alcohol, diazolidinylurea and parabens.
  • humectants glycerin and sorbitol .
  • the subject of the present invention is also the composition according to the invention as described above as a medicament .
  • the invention also relates to the use of the composition according to the invention as described above in the pharmaceutical and cosmetic field.
  • compositions of the invention are particularly suitable for the treatment and prevention of hyperpigmentary disorders such as melasma, chloasma, lentigines, senile lentigo, vitiligo, freckles, post- inflammatory hyperpigmentations due to an abrasion, a burn, a scar, a dermatosis, a contact allergy; naevi, hyperpigmentations with a genetic determinism, hyperpigmentations of metabolic or drug origin, melanomas or any other hyperpigmentary lesions.
  • hyperpigmentary disorders such as melasma, chloasma, lentigines, senile lentigo, vitiligo, freckles, post- inflammatory hyperpigmentations due to an abrasion, a burn, a scar, a dermatosis, a contact allergy; naevi, hyperpigmentations with a genetic determinism, hyperpigmentations of metabolic or drug
  • compositions according to the invention also find application in the cosmetic field, in particular in protection against the harmful effects of the sun, for preventing and/or combating photoinduced or chronologic ageing of the skin and of the superficial body growths .
  • the invention also relates to a method for a nontherapeutic cosmetic treatment for beautifying the skin and/or for improving its surface appearance, characterized in that a composition comprising adapalene and at least one depigmenting agent is applied to the skin and/or its superficial body growths .
  • Example 1 In the compositions below (Examples 1 to 5) , the proportions of the various constituents are expressed as a percentage by weight relative to the total weight of the composition.
  • Example 1 1 In the compositions below (Examples 1 to 5) , the proportions of the various constituents are expressed as a percentage by weight relative to the total weight of the composition.
  • Example 3 This composition should be applied once per day until complete depigmentation is obtained for the treatment of melasma.
  • Example 5 This composition should be applied twice per day until complete depigmentation is obtained for the treatment of melasma.
  • This composition should be applied once per day until complete depigmentation is obtained for the treatment of chloasma.
  • Example 6 Measurement of the depigmenting activity of the combination of adapalene and a depigmenting agent
  • the evaluation of the depigmenting and/or anti-pigmenting activity of hydroquinone 3% and Adapalene 0.1% alone or in combination for 8 weeks is carried out on the tail of SKH HR2 mice which is irradiated or not with ultraviolet B.
  • the tail of the SKH:HR2 mouse is naturally pigmented and this pigmentation increases under the effect of repeated UVB irradiation.
  • the depigmenting activity is measured on, the natural pigmentation after application of the test product to the tail of nonirradiated animals.
  • the anti-pigmenting activity is measured by the inhibition of the induction of the UV-induced pigmentation: the test product is applied to the tail of animals irradiated with UVB.
  • the treatment is carried out for 5 days per week for 8 weeks. 20 ⁇ l of test product, diluted in acetone, are applied to the tail in a deferred manner: hydroquinone in the morning and adapalene 4 h later. On the days for irradiation, the treatment is applied after irradiation.
  • the animals are irradiated 3 times per week for 8 weeks (Monday, Wednesday, Friday) at the dose of 90 mJ/cm 2 of UVB.
  • the evaluation is made by different clinical observations: once per week before irradiation, the pigmentation is evaluated by virtue of a score on a scale from 0 to .
  • the distribution of the scores is the following:
  • Figure 1 represents the kinetics for the scores of pigmentation of the mouse skin as a function of the treatment time with or without irradiation with ultraviolet B (up to 8 weeks of treatment) with ( ⁇ ) UVB + acetone, ( ⁇ ) UVB + Adapalene, ( ) UVB + hydroquinone, (•) UVB+hydroquinone+adapalene, (D] non- irradiated skin + acetone, ( ⁇ ) nonirridiated skin + adapalene (o) nonirradiated skin + hydroquinone (V) nonirradiated skin + hydroquinone + adapalene.
  • Figure 2 represents the pigmentation scores at the end of the study (D57) with (D] acetone, ( ⁇ U) hydroquinone, 13 adapalene, adapalene + hydroquinone with or without ultraviolet B irradiation.
  • Depigmenting activity hydroquinone alone at 3% induces a clinically visible depigmentation from the 6th week of treatment (D43) and a statistically significant depigmentation at the end of the study.
  • Adapalene alone does not modify the natural pigmentation. When adapalene is combined with Hydroquinone, it potentiates its depigmenting activity.
  • hydroquinone shows an anti- pigmenting effect at the 6th and at the 7th week (D50) which becomes less marked at the end of the study.
  • the adapalene + hydroquinone combination inhibits the pigmentation induced by UVB irradiation from its appearance and up to the end of the study where the difference is statistically significant ( ** ,p ⁇ 0.01).
  • the hydroquinone + adapalene combination exhibits a high antipigmenting activity and significantly inhibits the pigmentation induced by UVB irradiation from its appearance and up to the end of the study.
  • the hydroquinone + adapalene combination has a significant benefit as depigmenting agent in relation to hydroquinone alone.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Toxicology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Cosmetics (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/EP2003/010692 2002-09-05 2003-09-01 Depigmenting composition for the skin comprising adapalene and at least one depigmenting agent WO2004021967A2 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
AU2003270272A AU2003270272B2 (en) 2002-09-05 2003-09-01 Depigmenting composition for the skin comprising adapalene and at least one depigmenting agent
EP03750634A EP1536763B1 (en) 2002-09-05 2003-09-01 Depigmenting composition for the skin comprising adapalene and at least one depigmenting agent
DK03750634T DK1536763T3 (da) 2002-09-05 2003-09-01 Depigmenterende sammensætning til huden omfattende adapalen og mindst ét depigmenterende middel
DE60314887T DE60314887T2 (de) 2002-09-05 2003-09-01 Zusammensetzung zur depigmentierung der haut, die adapalen und mindestens ein depigmentierungsmittel enthält
BRPI0313370-2A BR0313370B1 (pt) 2002-09-05 2003-09-01 Composição despigmentante para a pele, uso de uma composição despigmentante para a pele, uso cosmético da mesma e método para tratamento cosmético não-terapêutico
JP2004533511A JP4662769B2 (ja) 2002-09-05 2003-09-01 アダパレンおよび少なくとも一つの色素脱失剤を含む皮膚用色素脱失組成物
MXPA05002064A MXPA05002064A (es) 2002-09-05 2003-09-01 Composicion despigmentante de la piel que comprende adapaleno y al menos un agente despigmentante.
CA002495043A CA2495043A1 (en) 2002-09-05 2003-09-01 Depigmenting composition for the skin comprising adapalene and at least one depigmenting agent
SI200330872T SI1536763T1 (sl) 2002-09-05 2003-09-01 Depigmentacijski sestavek za koĹľo, ki vsebuje adapalen in vsaj eno depigmentacijsko sredstvo
US11/042,519 US20050163731A1 (en) 2002-09-05 2005-01-26 Skin depigmenting compositions comprising adapalene and at least one depigmenting active agent
ZA2005/01753A ZA200501753B (en) 2002-09-05 2005-03-01 Depigmenting composition for the skin comprising adapalene and at least one depigmenting agent

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0211022 2002-09-05
FR0211022 2002-09-05
US41135002P 2002-09-18 2002-09-18
US60/411,350 2002-09-18

Related Child Applications (1)

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US11/042,519 Continuation US20050163731A1 (en) 2002-09-05 2005-01-26 Skin depigmenting compositions comprising adapalene and at least one depigmenting active agent

Publications (2)

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WO2004021967A2 true WO2004021967A2 (en) 2004-03-18
WO2004021967A3 WO2004021967A3 (en) 2005-02-17

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PCT/EP2003/010692 WO2004021967A2 (en) 2002-09-05 2003-09-01 Depigmenting composition for the skin comprising adapalene and at least one depigmenting agent

Country Status (19)

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US (1) US20050163731A1 (es)
EP (1) EP1536763B1 (es)
JP (1) JP4662769B2 (es)
KR (1) KR20050057238A (es)
CN (1) CN100391432C (es)
AT (1) ATE366566T1 (es)
AU (1) AU2003270272B2 (es)
BR (1) BR0313370B1 (es)
CA (1) CA2495043A1 (es)
CY (1) CY1107732T1 (es)
DE (1) DE60314887T2 (es)
DK (1) DK1536763T3 (es)
ES (1) ES2289315T3 (es)
MX (1) MXPA05002064A (es)
PL (1) PL377106A1 (es)
PT (1) PT1536763E (es)
RU (1) RU2317066C2 (es)
WO (1) WO2004021967A2 (es)
ZA (1) ZA200501753B (es)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004052353A2 (en) * 2002-12-12 2004-06-24 Galderma Research & Development, Snc Aqueous-alcoholic depigmenting gel containing a phenolic derivative and a retinoid
FR2871377A1 (fr) * 2004-06-11 2005-12-16 Galderma Res & Dev Gel depigmentant hydroalcoolique comprenant du mequinol et de l'adapalene
FR2890314A1 (fr) * 2005-09-02 2007-03-09 Galderma Res & Dev Compositiondepigmentante de la peau comprenant de l'adapalene au moins un agent depigmentant et au moins un agent anti-inflammatoire
WO2007052157A2 (en) * 2005-09-02 2007-05-10 Galderma Research & Development Depigmenting composition for the skin, comprising adapalene, at least one depigmenting agent and at least one anti-inflammatory agent
FR2894820A1 (fr) * 2005-12-15 2007-06-22 Galderma Res & Dev Compositions comprenant au moins un compose retinoide et au moins un compose anti-irritant et leurs utilisations
FR2915682A1 (fr) * 2007-05-04 2008-11-07 Galderma Res & Dev Compositions depigmentantes dermatologiques et cosmetiques, leurs procedes de preparation, et leurs utilisations
US7544674B2 (en) 2002-10-25 2009-06-09 Galderma S.A. Topical skin care composition
US20110144213A1 (en) * 2008-05-30 2011-06-16 Claire Mallard Anhydrous depigmenting compositions comprising a solubilized phenolic compound
US20110152372A1 (en) * 2008-05-30 2011-06-23 Galderma Research & Development Anhydrous petroleum jelly/elastomer-free depigmenting compositions comprising a solubilized phenolic compound and a retinoid
WO2011135090A1 (en) * 2010-04-29 2011-11-03 Galderma Research & Development Method for treating scars with adapalene 0.3%
GB2568758A (en) * 2017-11-28 2019-05-29 Chitty Nicholas Sun protection and acne treatment and prevention composition

Families Citing this family (8)

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Publication number Priority date Publication date Assignee Title
FR2910320B1 (fr) 2006-12-21 2009-02-13 Galderma Res & Dev S N C Snc Emulsion comprenant au moins un retinoide et du peroxyde de benzole
FR2910321B1 (fr) 2006-12-21 2009-07-10 Galderma Res & Dev S N C Snc Gel creme comprenant au moins un retinoide et du peroxyde de benzole
JP5646129B2 (ja) * 2007-03-31 2014-12-24 大正製薬株式会社 アダパレン含有外用剤組成物
US9364424B2 (en) * 2007-11-19 2016-06-14 Stiefel Laboratories, Inc. Topical cosmetic skin lightening compositions and methods of use thereof
FR2949065B1 (fr) 2009-08-17 2011-10-21 Natura Cosmeticos Sa Complexe eclaircissant la peau, utilisation dudit complexe, composition cosmetique ou pharmaceutique comprenant ledit complexe et procede pour son application
FR2969492B1 (fr) * 2010-12-23 2013-07-05 Galderma Res & Dev Mousses dermatologiques obtenues a partir d'un gel ou d'une suspension contenant de l'adapalene
RU2450836C1 (ru) * 2011-03-15 2012-05-20 Закрытое акционерное общество Фармацевтическое научно-производственное предприятие "Ретиноиды" Комбинированная мазевая композиция для уменьшения интенсивности локальной гиперпигментации кожи
US20220211597A1 (en) * 2021-01-07 2022-07-07 Actera Ingredients, Inc. Lipophilic third generation retinoid

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FR2871377A1 (fr) * 2004-06-11 2005-12-16 Galderma Res & Dev Gel depigmentant hydroalcoolique comprenant du mequinol et de l'adapalene
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US20110152372A1 (en) * 2008-05-30 2011-06-23 Galderma Research & Development Anhydrous petroleum jelly/elastomer-free depigmenting compositions comprising a solubilized phenolic compound and a retinoid
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AU2003270272A1 (en) 2004-03-29
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CN100391432C (zh) 2008-06-04
KR20050057238A (ko) 2005-06-16
US20050163731A1 (en) 2005-07-28
ES2289315T3 (es) 2008-02-01
BR0313370B1 (pt) 2015-02-24
WO2004021967A3 (en) 2005-02-17
CN1681473A (zh) 2005-10-12
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ZA200501753B (en) 2007-01-31
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